THERE ARE TWO interesting things about the 2014 Jeep Cherokee: The first is that the Trailhawk Edition ($36,120 as tested) with the 3.2-liter V6, nine-speed transmission, two-speed transfer case and locking rear differential, is a huge bargain to those buyers who know, for instance, what a locking rear differential is. When I call your name please raise your duck call.

Vehicles in this segment—car-based crossovers around $30,000, humps like the Toyota RAV4, Honda CR-V and Ford Escape—typically don't have the belly for...